JPH09505280A - シクロアルカンジオールおよびキラル化合物の調製におけるその使用 - Google Patents

シクロアルカンジオールおよびキラル化合物の調製におけるその使用

Info

Publication number: JPH09505280A
Authority: JP; Japan
Prior art keywords: dihydroxylation; compound; solution; mmol; compound according
Prior art date: 1993-10-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP7510703A

Other languages

English (en)

Japanese (ja)

Inventor

マッケイグ、レイモンド

ルークロフト、グラハム

パルマー、クリストファー

Original Assignee

カイロサイエンス・リミテッド

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-10-07

Filing date

1994-10-07

Publication date

1997-05-27

1994-10-07 Application filed by カイロサイエンス・リミテッド filed Critical カイロサイエンス・リミテッド

1997-05-27 Publication of JPH09505280A publication Critical patent/JPH09505280A/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 5
238000005906 dihydroxylation reaction Methods 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract 2
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
-1 for example Chemical group 0.000 claims description 10
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000962 organic group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
230000000903 blocking effect Effects 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical group FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
125000000524 functional group Chemical group 0.000 claims 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
229940124597 therapeutic agent Drugs 0.000 claims 1
230000000707 stereoselective effect Effects 0.000 abstract description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 14
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 8
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
239000012285 osmium tetroxide Substances 0.000 description 8
229910000489 osmium tetroxide Inorganic materials 0.000 description 8
239000007858 starting material Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
150000003857 carboxamides Chemical class 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000002243 precursor Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 3
NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical compound CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000005833 cis-dihydroxylation reaction Methods 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DDUFYKNOXPZZIW-UHFFFAOYSA-N 3-azabicyclo[2.2.1]hept-5-en-2-one Chemical compound C1C2C(=O)NC1C=C2 DDUFYKNOXPZZIW-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000003275 alpha amino acid group Chemical group 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001717 carbocyclic compounds Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
DSLSPCZKJILYBT-UHFFFAOYSA-N cyclopentene-1-carboxamide Chemical compound NC(=O)C1=CCCC1 DSLSPCZKJILYBT-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000004702 methyl esters Chemical group 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/59—Polyamides; Polyimides
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/61—Polyamines polyimines
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Textile Engineering (AREA)
Life Sciences & Earth Sciences (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP7510703A 1993-10-07 1994-10-07 シクロアルカンジオールおよびキラル化合物の調製におけるその使用 Pending JPH09505280A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB939320643A GB9320643D0 (en)	1993-10-07	1993-10-07	Preparation of chiral compounds
GB9320643.1		1993-10-07
PCT/GB1994/002194 WO1995009839A1 (en)	1993-10-07	1994-10-07	Cycloalkanediols and their use in preparing chiral compounds

Publications (1)

Publication Number	Publication Date
JPH09505280A true JPH09505280A (ja)	1997-05-27

Family

ID=10743134

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7510703A Pending JPH09505280A (ja)	1993-10-07	1994-10-07	シクロアルカンジオールおよびキラル化合物の調製におけるその使用

Country Status (10)

Country	Link
US (1)	US5739332A (de)
EP (1)	EP0722437B1 (de)
JP (1)	JPH09505280A (de)
AT (1)	ATE183736T1 (de)
AU (1)	AU683500B2 (de)
CA (1)	CA2172805A1 (de)
DE (1)	DE69420276T2 (de)
ES (1)	ES2134958T3 (de)
GB (1)	GB9320643D0 (de)
WO (1)	WO1995009839A1 (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8826205D0 (en) *	1988-11-09	1988-12-14	Wellcome Found	Heterocyclic compounds
US5217982A (en) *	1990-09-25	1993-06-08	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Compounds having antihypertensive properties

1993
- 1993-10-07 GB GB939320643A patent/GB9320643D0/en active Pending
1994
- 1994-10-07 ES ES94928493T patent/ES2134958T3/es not_active Expired - Lifetime
- 1994-10-07 JP JP7510703A patent/JPH09505280A/ja active Pending
- 1994-10-07 US US08/615,180 patent/US5739332A/en not_active Expired - Fee Related
- 1994-10-07 CA CA002172805A patent/CA2172805A1/en not_active Abandoned
- 1994-10-07 DE DE69420276T patent/DE69420276T2/de not_active Expired - Fee Related
- 1994-10-07 AT AT94928493T patent/ATE183736T1/de not_active IP Right Cessation
- 1994-10-07 EP EP94928493A patent/EP0722437B1/de not_active Expired - Lifetime
- 1994-10-07 WO PCT/GB1994/002194 patent/WO1995009839A1/en not_active Ceased
- 1994-10-07 AU AU77910/94A patent/AU683500B2/en not_active Ceased

Also Published As

Publication number	Publication date
DE69420276D1 (de)	1999-09-30
DE69420276T2 (de)	1999-12-09
WO1995009839A1 (en)	1995-04-13
AU7791094A (en)	1995-05-01
AU683500B2 (en)	1997-11-13
EP0722437A1 (de)	1996-07-24
ATE183736T1 (de)	1999-09-15
US5739332A (en)	1998-04-14
CA2172805A1 (en)	1995-04-13
ES2134958T3 (es)	1999-10-16
GB9320643D0 (en)	1993-11-24
EP0722437B1 (de)	1999-08-25

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